Acid-catalysed reactions of N-(diphenylmethylene)methylthiomethyl-amine N-oxide and O-(methylthiomethyl)benzophenone oxime

Abstract

Reactions of the title compounds with trichloroacetic acid, in the absence and presence of water, have been studied by n.m.r. spectroscopy. Most of the products have been identified, and mechanisms are suggested which involve initial protonation on oxygen followed by steps that are determined by the various nucleophiles present. Under dry conditions, the nitrone isomerises to the O-ether. Under most conditions, the nitrone forms NN-bis-methyl-thiomethylhydroxylamine. Reactions with dry hydrogen chloride have been briefly investigated.